Been there, it does not seem like a Microsoft problem. I have read many threads and I am not the only one. Yes I like Lion however it is not stable yet.
This proble is a Apple problem and no matter how many calls they are not able to assist. Number one they are not supporting a third party software. Yes I understand that. However the system is able to support different email clients with diff setup with authentication.
So here is the problem. No matter what option I choose for email clients ( Outlook or Thunderrbird) SMTP will not authenticate.
Mail Server is handling built in email client program ok with some upfront issues like cant use koberos authentication or if I enable SSL on SMTP it only works if I choose (use) option not (required) from the tab.
So I know its the mail server.
Ill make your wish come trough!
Kerio Connect is the best mac alternative for outlook users, supports EWS standard 99,8% and is easy to implement and maintain.
10.4 mailserver crash
10.5 mailserver crash
10.6 mailserver multible crashes
Gave up Apples mailserver
Kerio Connect works like a charm!
check the SMTP-port in your settings.
For SMTP you use normally port 25, for SSL port 995 (but also depending on your ISP).
But Lion Server use SMTP-port 25 and 587 (https://help.apple.com/advancedserveradmin/mac/10.7/#apdCA9A73CE-5F0C-4BDC-93E8- 2952C362FA3E)
So check your Outlook configuration - if you are using SSL for SMTP, try it without SSL (so port 25, if it's possible, depending on your athentification) - this has to work.
But don't forget to check your certificate-settings. Open your serversoftware - go to your server - 'network' where you can change your certificate-settings. Check if the certificate is enabled/disabled (if you use your certificate, you can use SSL ONLY - you can't use SSL and 'no SSL' at the same time - if you can do twice, please tell my how).
If it's running, try SSL again and change the port for what it's needed.
Otherwise you can also check you firewall settings.
Check if your SMTP-SSL-port is opened (in your server's firewall) and check your portforwarding...sometimes there are a lot of mistakes made.
But I'm fascinated that you mail server is running!!!
How do you get your mails from ISP to your server - I don't know how to configure.
I can't find the setting where I can fetch my mails (I am using the server-tool and server-admin software)
Thank you and good luck